TWI739289B - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- TWI739289B TWI739289B TW109102260A TW109102260A TWI739289B TW I739289 B TWI739289 B TW I739289B TW 109102260 A TW109102260 A TW 109102260A TW 109102260 A TW109102260 A TW 109102260A TW I739289 B TWI739289 B TW I739289B
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
本說明書主張於2019年1月21日在韓國智慧財產局提出申請的韓國專利申請案第10-2019-0007477號的優先權及權利，所述韓國專利申請案的全部內容併入本案供參考。 This specification claims the priority and rights of Korean Patent Application No. 10-2019-0007477 filed with the Korean Intellectual Property Office on January 21, 2019, and the entire content of the Korean patent application is incorporated into this case for reference.
本申請案是有關於一種化合物及一種包括其之有機發光元件。 This application relates to a compound and an organic light emitting device including the compound.
一般而言，有機發光現象指藉由使用有機材料將電能轉換成光能的現象。使用有機發光現象的有機發光元件通常具有包括第一電極、第二極及夾置於二者之間的有機材料層的結構。此處，所述有機材料層在許多情況下具有由不同材料構成的多層式結構(multi-layered structure)以提高有機發光元件的效率及穩定性，且舉例而言，可由電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層等構成。在有機發光元件的結構中，若在兩個電極之間施加電壓，則電洞會自第一電極注入所述有機材料層且電子會自第二電極注入所述有機材料層，且當所注入的電洞與 電子彼此相遇時，會形成激子，且當激子再次降至基態(ground state)時會發光。 Generally speaking, the organic luminescence phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic light-emitting element using an organic light-emitting phenomenon generally has a structure including a first electrode, a second electrode, and an organic material layer sandwiched between the two. Here, the organic material layer has a multi-layered structure composed of different materials in many cases to improve the efficiency and stability of the organic light-emitting element, and for example, it can be formed by a hole injection layer, an electric Hole transport layer, light-emitting layer, electron transport layer, electron injection layer, etc. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes will be injected into the organic material layer from the first electrode and electrons will be injected into the organic material layer from the second electrode, and when the injected Electric hole and When electrons meet each other, excitons are formed, and they emit light when they fall to the ground state again.
持續需要開發一種用於上述有機發光元件的新材料。 There is a continuing need to develop a new material for the above-mentioned organic light emitting element.
本申請案致力於提供一種化合物以及一種包括其之有機發光元件。 This application is dedicated to providing a compound and an organic light emitting device including the compound.
本申請案提供一種由以下式1表示的化合物。 This application provides a compound represented by Formula 1 below.
在式1中，R1至R4各自獨立地為氫；或氘，
R5及R6各自獨立地為經取代或未經取代的芳基；或者經取代或未經取代的雜環基，a為1至6的整數，b及d各自獨立地為1至4的整數，c為1至2的整數，當a至d各自獨立地為2或大於2的整數時，括弧中的取代基彼此相同或不同，且當b至d各自獨立地為2或大於2時，二或更多個R2至R4能夠各自獨立地鍵結至相鄰的基團以形成環。
In
此外，本申請案提供一種有機發光元件，所述有機發光元件包括：第一電極；第二電極，設置成面對所述第一電極；以及具有一或多個層的有機材料層，設置於所述第一電極與所述第二電極之間，其中所述有機材料層中的一或多個層包含上述化合物。 In addition, the present application provides an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode arranged to face the first electrode; and an organic material layer having one or more layers arranged in Between the first electrode and the second electrode, one or more of the organic material layers include the above-mentioned compound.
使用根據本申請案示例性實施例的化合物的有機發光元件可具有低驅動電壓、高發光效率或長使用壽命。 The organic light emitting element using the compound according to the exemplary embodiment of the present application may have a low driving voltage, high light emitting efficiency, or long service life.
1:基板 1: substrate
2:第一電極 2: The first electrode
3:發光層 3: luminescent layer
4:第二電極 4: second electrode
5:電洞注入層 5: Hole injection layer
6:電洞傳輸層 6: Hole transmission layer
7:電子阻擋層 7: Electron blocking layer
8:電洞阻擋層 8: Hole barrier layer
9:電子注入及傳輸層 9: Electron injection and transport layer
圖1示出基板1、第一電極2、發光層3及第二電極4依序堆疊的有機發光元件的實例。
FIG. 1 shows an example of an organic light-emitting element in which a
圖2示出基板1、第一電極2、電洞注入層5、電洞傳輸層6、電子阻擋層7、發光層3、電洞阻擋層8、電子注入及傳輸層9以及第二電極4依序堆疊的有機發光元件的實例。
2 shows the
以下，將更詳細地闡述本說明書。 Hereinafter, this specification will be explained in more detail.
本說明書提供由式1表示的化合物。 This specification provides a compound represented by Formula 1.
根據本申請案的示例性實施例，由式1表示的化合物具有能夠藉由具有如上所述的核心結構來調節三重態能量的優點，且可表現出長使用壽命及高效率特性。 According to an exemplary embodiment of the present application, the compound represented by Formula 1 has the advantage of being able to adjust the triplet energy by having the core structure as described above, and can exhibit long service life and high efficiency characteristics.
下文闡述本說明書中的取代基的實例，但不限於此。 Examples of substituents in this specification are described below, but are not limited thereto.
用語「取代」意指將鍵結至化合物的碳原子的氫原子變為另一取代基，且待被取代的位置不受限制，只要所述位置是氫原子被取代的位置(亦即，取代基可被取代的位置)，且當二或更多個被取代時，所述二或更多個取代基可彼此相同或不同。 The term "substitution" means to change the hydrogen atom bonded to the carbon atom of the compound to another substituent, and the position to be substituted is not limited, as long as the position is the position where the hydrogen atom is substituted (that is, the substitution The position where the group may be substituted), and when two or more are substituted, the two or more substituents may be the same or different from each other.
在本說明書中，用語「經取代或未經取代」意指經選自由氫；鹵素基；腈基；硝基；羥基；經取代或未經取代的烷基；經取代或未經取代的環烷基；經取代或未經取代的烯基；經取代或未經取代的胺基；經取代或未經取代的芳基；及經取代或未經取代的雜環基組成的群組中的一個或者二或更多個取代基取代，或經以上例示的取代基中連接有二或更多個取代基的取代基取代，或者沒有取代基。舉例而言，「連接有二或更多個取代基的取 代基」可為聯苯基。亦即，所述聯苯基亦可為芳基，且可被解釋為連接有兩個苯基的取代基。 In this specification, the term "substituted or unsubstituted" means a ring selected from hydrogen; halogen group; nitrile group; nitro group; hydroxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted ring Alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted amine; substituted or unsubstituted aryl; and substituted or unsubstituted heterocyclic group One or two or more substituents are substituted, or substituted with a substituent to which two or more substituents are connected among the above-exemplified substituents, or there is no substituent. For example, "A choice with two or more substituents attached "Substitute" may be biphenyl. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent to which two phenyl groups are connected.
在本說明書中，鹵素基的實例包括氟、氯、溴或碘。 In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.
在本說明書中，烷基可為直鏈的或支鏈的，且其碳原子的數目無特別限制，但較佳為1至50。其具體實例包括甲基、乙基、丙基、正丙基、異丙基、丁基、正丁基、異丁基、第三丁基、第二丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、異戊基、新戊基、第三戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、環戊基甲基、環己基甲基、辛基、正辛基、第三辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、異己基、2-甲基戊基、4-甲基己基、5-甲基己基等，但不限於此。 In this specification, the alkyl group may be linear or branched, and the number of its carbon atoms is not particularly limited, but it is preferably 1-50. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, second butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl , N-octyl, tertiary octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl Group, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited thereto.
在本說明書中，環烷基無特別限制，但較佳地具有3至60個碳原子，且其具體實例包括環丙基、環丁基、環戊基、3-甲基環戊基、2,3-二甲基環戊基、環己基、3-甲基環己基、4-甲基環己基、2,3-二甲基環己基、3,4,5-三甲基環己基、4-第三丁基環己基、環庚基、環辛基等，但不限於此。 In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2 ,3-Dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4 -Tertiary butyl cyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited thereto.
在本說明書中，所述烯基可為直鏈的或支鏈的，且其碳原子的數目無特別限制，但較佳為2至40。其具體實例包括乙烯基、1-丙烯基、異丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯 丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-雙(二苯基-1-基)乙烯基-1-基、二苯乙烯基(stilbenyl group)、苯乙烯基(styrenyl group)等，但不限於此。 In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but it is preferably 2-40. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentene Group, 3-methyl-1-butenyl, 1,3-butadienyl, alkene Propyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl- 1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., But it is not limited to this.
在本說明書中，當芳基為單環芳基時，其碳原子的數目無特別限制，但較佳為6至25。單環芳基的具體實例包括苯基、聯苯基、三聯苯基等，但不限於此。 In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6-25. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, etc., but are not limited thereto.
當芳基為多環芳基時，其碳原子的數目無特別限制，但較佳為10至24。所述多環芳基的具體實例包括萘基、蒽基、菲基、芘基、苝基、
在本說明書中，芴基可被取代，且相鄰的取代基可彼此鍵結而形成環。 In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
當芴基被取代時，取代基可為
在本說明書中，雜環基包含除碳外的一或多個原子(即，一或多個雜原子)，且具體而言，所述雜原子可包括選自由O、N、Se、S等組成的群組中的一或多個原子。所述雜環基的碳原子的數目無特別限制，但較佳為2至60。雜環基的實例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、***基、吡啶基、聯吡啶基、嘧啶基、三嗪基、***基、吖啶基、噠嗪基、 吡嗪基、喹啉基(qinolinyl group)、喹唑啉基、喹噁啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、異喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、啡啉基、噻唑基、異噁唑基、噁二唑基、噻二唑基、苯并噻唑基、啡噻嗪基、二苯并呋喃基等，但不限於此。 In the present specification, the heterocyclic group includes one or more atoms (ie, one or more heteroatoms) other than carbon, and specifically, the heteroatom may include selected from O, N, Se, S, etc. One or more atoms in a group. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2-60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazole Group, acridinyl, pyridazinyl, Pyrazinyl, qinolinyl group, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indole Dolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthryl, thiazole But not limited thereto.
在本說明書中，胺基可選自由以下組成的群組：-NH2；烷基胺基；N-烷基芳基胺基；芳基胺基；N-芳基雜芳基胺基；N-烷基雜芳基胺基；以及雜芳基胺基，且其碳原子的數目無特別限制，但較佳為1至30。胺基的具體實例包括甲胺基、二甲胺基、乙胺基、二乙胺基、苯胺基、萘胺基、聯苯胺基、蒽胺基、9-甲基-蒽胺基、二苯胺基、N-苯基萘胺基、二甲苯胺基、N-苯基甲苯胺基、三苯胺基、N-苯基聯苯胺基、N-苯基萘胺基、N-聯苯基萘胺基、N-萘基芴胺基、N-苯基菲胺基、N-聯苯基菲胺基、N-苯基芴胺基、N-苯基三聯苯胺基、N-菲基芴胺基、N-聯苯基芴胺基等，但不限於此。 In this specification, the amino group can be selected from the group consisting of: -NH 2 ; alkylamino group; N-alkylarylamino group; arylamino group; N-arylheteroarylamino group; N -Alkylheteroarylamino; and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1-30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, anilino, naphthylamino, benzidine, anthracene, 9-methyl-anthracene, and diphenylamine Group, N-phenylnaphthylamino, xylanilin, N-phenyltolylin, triphenylamino, N-phenylbenzidine, N-phenylnaphthylamino, N-biphenylnaphthylamine Group, N-naphthyl fluorenyl amino group, N-phenyl phenanthryl amino group, N-biphenyl phenanthryl amino group, N-phenyl fluoren amino group, N-phenyl terphenyl fluoren amino group, N-phenanthryl fluoren amino group , N-biphenyl fluorenylamine group, etc., but not limited to this.
在本說明書中，N-烷基芳基胺基意指其中烷基及芳基經胺基的N取代的胺基。 In the present specification, the N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted with N of an amino group.
在本說明書中，N-芳基雜芳基胺基意指其中芳基及雜芳基經胺基的N取代的胺基。 In the present specification, the N-arylheteroarylamino group means an amino group in which an aryl group and a heteroaryl group are N-substituted with an amino group.
在本說明書中，N-烷基雜芳基胺基意指其中烷基及雜芳基經胺基的N取代的胺基。 In the present specification, the N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are N-substituted with an amino group.
在本說明書中，上述對烷基、芳基及雜芳基的說明可分別適用於烷基胺基；N-烷基芳基胺基；芳基胺基；N-芳基雜芳基胺基；N-烷基雜芳基胺基及雜芳基胺基中的烷基、芳基及雜芳基。 In this specification, the above descriptions of alkyl, aryl and heteroaryl can be applied to alkylamino; N-alkylarylamino; arylamino; N-arylheteroarylamino, respectively ; Alkyl, aryl and heteroaryl in N-alkylheteroarylamine and heteroarylamine.
在本說明書中，「相鄰的」基團可意指經直接連接至其中對應取代基經取代的原子的原子所取代的取代基、在空間上最靠近對應取代基設置的取代基或經其中對應取代基經取代的原子所取代的另一取代基。舉例而言，取代於苯環中的鄰位處的兩個取代基以及經脂族環中的同一個碳取代的兩個取代基可被解釋為彼此「相鄰」的基團。 In the present specification, the "adjacent" group may mean a substituent substituted by an atom directly connected to the atom in which the corresponding substituent is substituted, a substituent disposed closest in space to the corresponding substituent, or The corresponding substituent is another substituent substituted by a substituted atom. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted with the same carbon in the aliphatic ring can be interpreted as groups "adjacent" to each other.
在本說明書中，相鄰的基團彼此鍵結以形成環的情況意謂相鄰的基團彼此鍵結以形成如上所述經取代或未經取代的烴環或者經取代或未經取代的雜環，可形成單環式環或多環式環，且所述環可為脂族環、芳族環或其稠合形式，且不限於此。 In this specification, the case where adjacent groups are bonded to each other to form a ring means that adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or substituted or unsubstituted hydrocarbon ring as described above. The heterocyclic ring may form a monocyclic ring or a polycyclic ring, and the ring may be an aliphatic ring, an aromatic ring or a condensed form thereof, and is not limited thereto.
在本說明書中，鍵結至相鄰的基團以形成環意謂鍵結至相鄰的基團以形成經取代或未經取代的脂族烴環；經取代或未經取代的芳族烴環；經取代或未經取代的脂族雜環；經取代或未經取代的芳族雜環；或其組合形式。 In this specification, bonding to an adjacent group to form a ring means bonding to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring; substituted or unsubstituted aromatic hydrocarbon Ring; substituted or unsubstituted aliphatic heterocyclic ring; substituted or unsubstituted aromatic heterocyclic ring; or a combination thereof.
在本說明書中，所述脂族烴環意指僅由碳原子及氫原子構成以作為不是芳族基的環的環。 In the present specification, the aliphatic hydrocarbon ring means a ring composed only of carbon atoms and hydrogen atoms as a ring that is not an aromatic group.
在本說明書中，除為二價芳族烴環以外，對芳基的上述說明可應用於芳族烴環。芳族烴環的實例包括苯環、萘環、蒽環等，但不限於此。 In this specification, in addition to the divalent aromatic hydrocarbon ring, the above description of the aryl group can be applied to the aromatic hydrocarbon ring. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, etc., but are not limited thereto.
在本說明書中，除了為二價雜環以外，對雜環基的上述說明可應用於雜環。 In this specification, in addition to being a divalent heterocyclic ring, the above description of the heterocyclic group can be applied to the heterocyclic ring.
在本說明書中，所述脂族雜環意指包含雜原子中的一或多者的脂族環。 In the present specification, the aliphatic heterocyclic ring means an aliphatic ring including one or more of heteroatoms.
在本說明書中，所述芳族雜環意指包含雜原子中的一或多者的芳族環。 In the present specification, the aromatic heterocyclic ring means an aromatic ring including one or more of heteroatoms.
由式1表示的所述化合物被選擇為以下式2至式4中的任一者。
The compound represented by
[式3]
在式2至式4中，R1至R6及a至d與式1中所定義的相同。
In
根據本申請案的示例性實施例，R1至R4各自獨立地為氫；或氘。 According to an exemplary embodiment of the present application, R1 to R4 are each independently hydrogen; or deuterium.
根據本申請案的示例性實施例，R1至R4為氫。 According to an exemplary embodiment of the present application, R1 to R4 are hydrogen.
根據本申請案的示例性實施例，當b至d各自獨立地為2 或大於2時，二或更多個R2至R4可各自獨立地鍵結至相鄰的基團以形成環。 According to an exemplary embodiment of the present application, when b to d are each independently 2 Or when it is greater than 2, two or more R2 to R4 may each independently bond to adjacent groups to form a ring.
根據本申請案的示例性實施例，當b為2或大於2時，二或更多個R2可鍵結至相鄰的基團以形成環。 According to an exemplary embodiment of the present application, when b is 2 or greater than 2, two or more R2 may be bonded to adjacent groups to form a ring.
根據本申請案的示例性實施例，當b為2或大於2時，二或更多個R2可鍵結至相鄰的基團以形成苯環。 According to an exemplary embodiment of the present application, when b is 2 or greater than 2, two or more R2 may be bonded to adjacent groups to form a benzene ring.
根據本申請案的示例性實施例，當c為2或大於2時，二或更多個R3可鍵結至相鄰的基團以形成環。 According to an exemplary embodiment of the present application, when c is 2 or greater than 2, two or more R3 may be bonded to adjacent groups to form a ring.
根據本申請案的示例性實施例，當c為2或大於2時，二或更多個R3可鍵結至相鄰的基團以形成苯環。 According to an exemplary embodiment of the present application, when c is 2 or greater than 2, two or more R3 may be bonded to adjacent groups to form a benzene ring.
根據本申請案的示例性實施例，當d為2或大於2時，二或更多個R4可鍵結至相鄰的基團以形成環。 According to an exemplary embodiment of the present application, when d is 2 or greater than 2, two or more R4 may be bonded to adjacent groups to form a ring.
根據本申請案的示例性實施例，當d為2或大於2時，二或更多個R4可鍵結至相鄰的基團以形成苯環。 According to an exemplary embodiment of the present application, when d is 2 or greater than 2, two or more R4 may be bonded to adjacent groups to form a benzene ring.
由式1表示的所述化合物被選擇為以下式2-1至式2-8、式3-1至式3-8及式4-1至式4-8中的任一者。
The compound represented by
[式2-1]
[式2-4]
[式2-6]
[式2-8]
[式3-2]
[式4-3]
[式4-8]
在式2-1至式2-8、式3-1至式3-8及式4-1至式4-8中，R4至R6及d與式1中所定義的相同，R7及R8各自獨立地為氫；或氘，e1及e2各自為0或1，且e1與e2之和為1及2，e為1至10的整數，且f為1至8的整數，當e為2或大於2時，多個R7彼此相同或不同，且當f為2或大於2時，多個R8彼此相同或不同。
In Formula 2-1 to Formula 2-8, Formula 3-1 to Formula 3-8, and Formula 4-1 to Formula 4-8, R4 to R6 and d are the same as defined in
根據本申請案的示例性實施例，R5及R6各自獨立地為具有6至60個碳原子的經取代或未經取代的芳基；或者具有2至60個碳原子的經取代或未經取代的雜環基。 According to an exemplary embodiment of the present application, R5 and R6 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted having 2 to 60 carbon atoms的heterocyclyl.
根據本申請案的示例性實施例，R5及R6各自獨立地為具有6至30個碳原子的經取代或未經取代的芳基；或者具有2至30個碳原子的經取代或未經取代的雜環基。 According to an exemplary embodiment of the present application, R5 and R6 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted having 2 to 30 carbon atoms的heterocyclyl.
根據本申請案的示例性實施例，R5及R6各自獨立地為具有6至15個碳原子的經取代或未經取代的芳基；或者具有2至 15個碳原子的經取代或未經取代的雜環基。 According to an exemplary embodiment of the present application, R5 and R6 are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; or having 2 to A substituted or unsubstituted heterocyclic group of 15 carbon atoms.
根據本申請案的示例性實施例，R5及R6各自獨立地為經取代或未經取代的苯基；經取代或未經取代的萘基；經取代或未經取代的聯苯基；經取代或未經取代的菲基；經取代或未經取代的咔唑基；經取代或未經取代的二苯并噻吩基；或者經取代或未經取代的二苯并呋喃基。 According to an exemplary embodiment of the present application, R5 and R6 are each independently substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted biphenyl; substituted Or unsubstituted phenanthrenyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzofuranyl.
根據本申請案的示例性實施例，R5及R6各自獨立地為苯基；萘基；聯苯基；菲基；未經取代或經苯基取代的咔唑基；二苯并噻吩基；或二苯并呋喃基。 According to an exemplary embodiment of the present application, R5 and R6 are each independently a phenyl group; naphthyl group; biphenyl group; phenanthryl group; unsubstituted or phenyl-substituted carbazolyl group; dibenzothienyl group; or Dibenzofuranyl.
此外，根據本申請案的示例性實施例，由式1表示的化合物為選自以下結構式中的任一者。
In addition, according to an exemplary embodiment of the present application, the compound represented by
此外，本說明書提供一種包含上述化合物的有機發光元件。 In addition, this specification provides an organic light-emitting element containing the above-mentioned compound.
本說明書的示例性實施例提供一種有機發光元件，所述有機發光元件包括：第一電極；第二電極，設置成面對所述第一 電極；以及具有一或多個層的有機材料層，設置於所述第一電極與所述第二電極之間，其中所述有機材料層中的一或多個層包含所述化合物。 Exemplary embodiments of this specification provide an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode arranged to face the first An electrode; and an organic material layer having one or more layers, disposed between the first electrode and the second electrode, wherein one or more layers in the organic material layer include the compound.
當在本說明書中一個構件設置於另一構件「上」時，此不僅包括其中所述一個構件與所述另一構件進行接觸的情況，且亦包括其中在所述兩個構件之間存在再一構件的情況。 When a member is placed "on" another member in this specification, this includes not only the case where the one member is in contact with the other member, but also the case where there is another member between the two members. The case of a component.
當在本說明書中一個部分「包括」一個組成部件時，除非另外具體闡述，否則此不意指另一組成部件被排除，而是意指可更包括另一組成部件。 When a part "includes" a component in this specification, unless specifically stated otherwise, this does not mean that another component is excluded, but it means that another component may be further included.
本說明書的所述有機發光元件的有機材料層亦可由單層式結構構成，但可由其中堆疊具有二或更多個層的有機材料層的多層式結構構成。舉例而言，本發明的有機發光元件可具有包括電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層等作為有機材料層的結構。然而，有機發光元件的結構不限於此，而是可包括更少數目的有機層。 The organic material layer of the organic light-emitting element described in this specification may also be composed of a single-layer structure, but may be composed of a multilayer structure in which organic material layers having two or more layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light emitting element is not limited to this, but may include a smaller number of organic layers.
在本說明書的示例性實施例中，有機材料層包括電洞注入層或電洞傳輸層，且所述電洞注入層或所述電洞傳輸層包含所述化合物。 In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
在本說明書的示例性實施例中，有機材料層包括發光層，且所述發光層包含所述化合物。 In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
在本說明書的示例性實施例中，有機材料層包括發光層，且所述發光層包含所述化合物作為主體。 In the exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host.
在本說明書的示例性實施例中，有機材料層包括發光層，且所述發光層包含式1的化合物作為第一主體，並且更包含由下式H表示的第二主體。
In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound of
在式H中，A為經取代或未經取代的萘環，Ar1為具有6至60個碳原子的經取代或未經取代的芳基，L1至L3各自獨立地為單鍵；或具有6至60個碳原子的經取代或未經取代的伸芳基，Ar2及Ar3各自獨立地為具有6至60個碳原子的經取代或未經取代的芳基；或者具有2至60個碳原子、包含N、O及S中的一或多個雜原子的經取代或未經取代的雜芳基，且p為0至9的整數。 In formula H, A is a substituted or unsubstituted naphthalene ring, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and L1 to L3 are each independently a single bond; or have 6 A substituted or unsubstituted aryl group having to 60 carbon atoms, Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or having 2 to 60 carbon atoms , A substituted or unsubstituted heteroaryl group containing one or more heteroatoms among N, O, and S, and p is an integer of 0-9.
在本說明書的示例性實施例中，A為經取代或未經取代的萘環。 In the exemplary embodiment of the present specification, A is a substituted or unsubstituted naphthalene ring.
在本說明書的示例性實施例中，A為未經取代或經氘取代的萘環。 In the exemplary embodiment of the present specification, A is a naphthalene ring that is unsubstituted or substituted with deuterium.
在本說明書的示例性實施例中，A為萘環。 In the exemplary embodiment of the present specification, A is a naphthalene ring.
在本說明書的示例性實施例中，p意指氘取代的數目，且其中p為0的情況意指全部被氫取代的狀態。 In the exemplary embodiment of the present specification, p means the number of deuterium substitutions, and the case where p is 0 means a state where all is substituted by hydrogen.
在本說明書的示例性實施例中，L1至L3各自獨立地為單鍵；或者具有6至30個碳原子的經取代或未經取代的伸芳基。 In the exemplary embodiment of the present specification, L1 to L3 are each independently a single bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
在本說明書的示例性實施例中，L1至L3各自獨立地為單鍵；經取代或未經取代的伸苯基；或者經取代或未經取代的萘基。 In the exemplary embodiment of the present specification, L1 to L3 are each independently a single bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthyl group.
在本說明書的示例性實施例中，L1至L3各自獨立地為單鍵；未經取代或經氘取代的伸苯基；或者未經取代或經氘取代的萘基。 In the exemplary embodiment of the present specification, L1 to L3 are each independently a single bond; a phenylene group that is unsubstituted or substituted with deuterium; or a naphthyl group that is unsubstituted or substituted with deuterium.
在本說明書的示例性實施例中，L1至L3各自獨立地為單鍵；伸苯基；或萘基。 In the exemplary embodiment of the present specification, L1 to L3 are each independently a single bond; a phenylene group; or a naphthyl group.
在本說明書的示例性實施例中，Ar1為具有6至30個碳原子的經取代或未經取代的芳基。 In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
在本說明書的示例性實施例中，Ar1為經取代或未經取代的苯基；經取代或未經取代的聯苯基；經取代或未經取代的三聯苯基；或者經取代或未經取代的萘基。 In the exemplary embodiment of the present specification, Ar1 is substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; or substituted or unsubstituted Substituted naphthyl.
在本說明書的示例性實施例中，Ar1為未取代或經選自由氘、烷基、環烷基及芳基組成的群組中的基團取代的苯基；未經取代或經選自由氘、烷基、環烷基及芳基組成的群組中的基團取代的聯苯基；未經取代或經選自由氘、烷基、環烷基及芳基組成 的群組中的基團取代的三聯苯基；或者未經取代或經選自由氘、烷基、環烷基及芳基組成的群組中的基團取代的萘基。 In the exemplary embodiment of the present specification, Ar1 is a phenyl group that is unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl, cycloalkyl, and aryl; unsubstituted or selected from deuterium Biphenyl substituted by a group in the group consisting of, alkyl, cycloalkyl and aryl; unsubstituted or selected from deuterium, alkyl, cycloalkyl and aryl Terphenyl substituted by a group in the group; or naphthyl substituted with a group selected from the group consisting of deuterium, alkyl, cycloalkyl, and aryl.
在本說明書的示例性實施例中，Ar1為未經取代或經選自由氘、烷基、環烷基及芳基組成的群組中的基團取代的苯基；聯苯基；三聯苯基；或萘基。 In the exemplary embodiment of the present specification, Ar1 is a phenyl group that is unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl, cycloalkyl, and aryl; biphenyl; terphenyl ; Or naphthyl.
在本說明書的示例性實施例中，Ar1為未經取代或經選自由氘、第三丁基、金剛烷基、苯基及萘基組成的群組中的基團取代的苯基；聯苯基；三聯苯基；或萘基。 In the exemplary embodiment of the present specification, Ar1 is a phenyl group that is unsubstituted or substituted with a group selected from the group consisting of deuterium, tertiary butyl, adamantyl, phenyl, and naphthyl; biphenyl Group; terphenyl; or naphthyl.
在本說明書的示例性實施例中，Ar2及Ar3各自獨立地為具有6至30個碳原子的經取代或未經取代的芳基；或者具有2至30個碳原子、包含N、O及S中的一或多個雜原子的經取代或未經取代的雜芳基。 In the exemplary embodiment of the present specification, Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or having 2 to 30 carbon atoms, including N, O, and S One or more heteroatoms in the substituted or unsubstituted heteroaryl group.
在本說明書的示例性實施例中，Ar2及Ar3各自獨立地為經取代或未經取代的苯基；經取代或未經取代的聯苯基；經取代或未經取代的三聯苯基；經取代或未經取代的萘基；經取代或未經取代的芴基；經取代或未經取代的二苯并呋喃基；或者經取代或未經取代的二苯并噻吩基。 In the exemplary embodiment of the present specification, Ar2 and Ar3 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothienyl.
在本說明書的示例性實施例中，Ar2及Ar3各自獨立地為未經取代或經選自由氘、烷基、環烷基及芳基組成的群組中的基團取代的苯基；未經取代或經氘取代的聯苯基；未經取代或經氘取代的三聯苯基；未經取代或經氘取代的萘基；未經取代或經烷基取代的芴基；未經取代或經氘取代的二苯并呋喃基；或者未經 取代或經氘取代的二苯并噻吩基。 In the exemplary embodiment of the present specification, Ar2 and Ar3 are each independently a phenyl group that is unsubstituted or substituted with a group selected from the group consisting of deuterium, alkyl, cycloalkyl, and aryl; Substituted or deuterium-substituted biphenyl; unsubstituted or deuterium-substituted terphenyl; unsubstituted or deuterium-substituted naphthyl; unsubstituted or alkyl-substituted fluorenyl; unsubstituted or substituted Deuterium-substituted dibenzofuranyl; or without Substituted or deuterium-substituted dibenzothienyl.
在本說明書的示例性實施例中，Ar2及Ar3各自獨立地為未經取代或經選自由氘、第三丁基、金剛烷基及苯基組成的群組中的基團取代的苯基；聯苯基；三聯苯基；萘基；二甲基芴基；二苯并呋喃基；或二苯并噻吩基。 In the exemplary embodiment of the present specification, Ar2 and Ar3 are each independently a phenyl group that is unsubstituted or substituted with a group selected from the group consisting of deuterium, tertiary butyl, adamantyl, and phenyl; Biphenyl; terphenyl; naphthyl; dimethylfluorenyl; dibenzofuranyl; or dibenzothienyl.
在本說明書的示例性實施例中，由式H表示的第二主體可由以下結構中的任一者表示，且不限於此。 In the exemplary embodiment of the present specification, the second body represented by Formula H may be represented by any of the following structures, and is not limited thereto.
在本說明書的示例性實施例中，有機材料層包括電子傳輸層或電子注入層，且所述電子傳輸層或所述電子注入層包含所述化合物。 In the exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
在本說明書的示例性實施例中，有機發光元件更包括選自由以下組成的群組中的一個層或者二或更多個層：電洞注入層、電洞傳輸層、電子傳輸層、電子注入層、電子阻擋層及電洞阻擋層。 In the exemplary embodiment of the present specification, the organic light emitting element further includes one layer or two or more layers selected from the group consisting of: hole injection layer, hole transport layer, electron transport layer, electron injection Layer, electron blocking layer and hole blocking layer.
在本申請案的示例性實施例中，有機發光元件包括：第一電極；第二電極，設置成面對所述第一電極；發光層，設置於所述第一電極與所述第二電極之間；以及具有二或更多個層的有機材料層，設置於所述發光層與所述第一電極之間或者所述發光 層與所述第二電極之間，其中所述有機材料層中的所述二或更多個層中的至少一者包含所述化合物。在本申請案的示例性實施例中，作為有機材料層的所述二或更多個層，二或更多者可選自由以下組成的群組：電子傳輸層、電子注入層、同時傳輸及注入電子的層以及電洞阻擋層。 In an exemplary embodiment of the present application, the organic light emitting element includes: a first electrode; a second electrode disposed to face the first electrode; a light emitting layer disposed on the first electrode and the second electrode And an organic material layer having two or more layers, disposed between the light-emitting layer and the first electrode or the light-emitting layer Between the layer and the second electrode, wherein at least one of the two or more layers in the organic material layer includes the compound. In the exemplary embodiment of the present application, as the two or more layers of the organic material layer, two or more can be selected from the group consisting of: electron transport layer, electron injection layer, simultaneous transport and The electron injection layer and the hole blocking layer.
在另一示例性實施例中，有機發光元件可為其中第一電極、具有一或多個層的有機材料層及第二電極依序堆疊在基板上的標準型有機發光元件。 In another exemplary embodiment, the organic light-emitting element may be a standard organic light-emitting element in which a first electrode, an organic material layer having one or more layers, and a second electrode are sequentially stacked on a substrate.
在再一示例性實施例中，有機發光元件可為其中第二電極、具有一或多個層的有機材料層及第一電極依序堆疊在基板上的倒置型有機發光元件。 In still another exemplary embodiment, the organic light-emitting element may be an inverted organic light-emitting element in which a second electrode, an organic material layer having one or more layers, and a first electrode are sequentially stacked on a substrate.
有機發光元件可具有例如下述堆疊結構，但所述堆疊結構不限於此。 The organic light emitting element may have, for example, the following stacked structure, but the stacked structure is not limited thereto.
(1)正電極/電洞傳輸層/發光層/負電極 (1) Positive electrode/hole transport layer/light-emitting layer/negative electrode
(2)正電極/電洞注入層/電洞傳輸層/發光層/負電極 (2) Positive electrode/hole injection layer/hole transport layer/light-emitting layer/negative electrode
(3)正電極/電洞傳輸層/發光層/電子傳輸層/負電極 (3) Positive electrode/hole transport layer/light emitting layer/electron transport layer/negative electrode
(4)正電極/電洞傳輸層/發光層/電子傳輸層/電子注入層/負電極 (4) Positive electrode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/negative electrode
(5)正電極/電洞注入層/電洞傳輸層/發光層/電子傳輸層/負電極 (5) Positive electrode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/negative electrode
(6)正電極/電洞注入層/電洞傳輸層/發光層/電子傳輸層/電子注入層/負電極 (6) Positive electrode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/negative electrode
(7)正電極/電洞傳輸層/電子阻擋層/發光層/電子傳輸層/負電極 (7) Positive electrode/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/negative electrode
(8)正電極/電洞傳輸層/電子阻擋層/發光層/電子傳輸層/電子注入層/負電極 (8) Positive electrode/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/electron injection layer/negative electrode
(9)正電極/電洞注入層/電洞傳輸層/電子阻擋層/發光層/電子傳輸層/負電極 (9) Positive electrode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/negative electrode
(10)正電極/電洞注入層/電洞傳輸層/電子阻擋層/發光層/電子傳輸層/電子注入層/負電極 (10) Positive electrode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / negative electrode
(11)正電極/電洞傳輸層/發光層/電洞阻擋層/電子傳輸層/負電極 (11) Positive electrode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/negative electrode
(12)正電極/電洞傳輸層/發光層/電洞阻擋層/電子傳輸層/電子注入層/負電極 (12) Positive electrode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/negative electrode
(13)正電極/電洞注入層/電洞傳輸層/發光層/電洞阻擋層/電子傳輸層/負電極 (13) Positive electrode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/negative electrode
(14)正電極/電洞注入層/電洞傳輸層/發光層/電洞阻擋層/電子傳輸層/電子注入層/負電極 (14) Positive electrode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/negative electrode
(15)正電極/電洞注入層/電洞傳輸層/電子阻擋層/發光層/電洞阻擋層/電子傳輸層/電子注入層/負電極 (15) Positive electrode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/negative electrode
(16)正電極/電洞注入層/電洞傳輸層/電子阻擋層/發光層/電洞阻擋層/電子傳輸及注入層/負電極 (16) Positive electrode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport and injection layer/negative electrode
舉例而言，根據本說明書的示例性實施例的有機發光元件的結構例示於圖1及圖2中。 For example, the structure of the organic light emitting element according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.
圖1例示基板1、第一電極2、發光層3及第二電極4依序堆疊的有機發光元件的結構。在上述結構中，化合物可包含於發光層3中。
FIG. 1 illustrates the structure of an organic light emitting element in which a
圖2例示基板1、第一電極2、電洞注入層5、電洞傳輸層6、電子阻擋層7、發光層3、電洞阻擋層8、電子注入及傳輸層9以及第二電極4依序堆疊的有機發光元件的結構。在上述結構中，化合物可包含於電洞注入層5、電洞傳輸層6、電子阻擋層7、發光層3、電洞阻擋層8以及電子注入及傳輸層9中的一或多個層中。在上述結構中，化合物可包含於發光層3中。
2 illustrates the
除有機材料層的一或多個層包含本說明書的化合物(即，所述化合物)外，本說明書的有機發光元件可藉由此項技術中已知的材料及方法來製造。 Except that one or more layers of the organic material layer include the compound of the specification (ie, the compound), the organic light-emitting device of the specification can be manufactured by materials and methods known in the art.
當有機發光元件包括多個有機材料層時，所述有機材料層可由同種材料或不同材料形成。 When the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
除有機材料層的一或多個層包含所述化合物(即，由式1表示的化合物)外，本說明書的有機發光元件可藉由此項技術中已知的材料及方法來製造。 Except that one or more layers of the organic material layer include the compound (ie, the compound represented by Formula 1), the organic light-emitting device of the present specification can be manufactured by materials and methods known in the art.
舉例而言，本說明書的有機發光元件可藉由在基板上依序堆疊第一電極、有機材料層及第二電極而製造。在此種情況下，有機發光元件可藉由以下方式來製造：藉由使用例如濺射或電子束蒸發等物理氣相沈積(physical vapor deposition，PVD)方法在基板上沈積具有導電性的金屬或金屬氧化物或者其合金而形成第 一電極，在其上形成包括電洞注入層、電洞傳輸層、發光層及電子傳輸層的有機材料層，然後在其上沈積可用作第二極的材料。除上述方法以外，可藉由在基板上依序沈積第二電極材料、有機材料層及第一電極材料來製作有機發光元件。 For example, the organic light emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting element can be manufactured by the following method: by using physical vapor deposition (physical vapor deposition, PVD) methods such as sputtering or electron beam evaporation to deposit conductive metal or Metal oxides or their alloys form the first An electrode on which an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer is formed, and then a material that can be used as a second electrode is deposited on it. In addition to the above methods, the organic light-emitting device can be fabricated by sequentially depositing the second electrode material, the organic material layer, and the first electrode material on the substrate.
此外，當製造有機發光元件時，所述式1的化合物不僅可藉由真空沈積方法(vacuum deposition method)而且亦可藉由溶液施加法(solution application method)而形成為有機材料層。此處，溶液施加法意指旋塗(spin coating)、浸塗(dip coating)、刮刀塗佈(doctor blading)、噴墨印刷(inkjet printing)、網版印刷(screen printing)、噴射法(spray method)、輥塗(roll coating)等，但不限於此。
In addition, when manufacturing an organic light-emitting element, the compound of
除上述方法以外，有機發光元件亦可藉由在基板上依序沈積第二電極材料、有機材料層及第一電極材料而製作(國際公開案第2003/012890號)。然而，製造方法不限於此。 In addition to the above methods, organic light-emitting devices can also be fabricated by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate (International Publication No. 2003/012890). However, the manufacturing method is not limited to this.
在本說明書的示例性實施例中，所述第一電極為正電極，且所述第二電極為負電極。 In the exemplary embodiment of this specification, the first electrode is a positive electrode, and the second electrode is a negative electrode.
在另一示例性實施例中，所述第一電極為負電極，且所述第二電極為正電極。 In another exemplary embodiment, the first electrode is a negative electrode, and the second electrode is a positive electrode.
作為第一電極材料，通常較佳的是具有高的功函數的材料以有利於將電洞注入有機材料層中。可用於本發明的第一極材料的具體實例包括：金屬，例如釩、鉻、銅、鋅及金或其合金；金屬氧化物，例如氧化鋅、氧化銦、氧化銦錫(indium tin oxide， ITO)及氧化銦鋅(indium zinc oxide，IZO)；金屬與氧化物的組合，例如ZnO：Al或SnO2：Sb；導電聚合物，例如聚(3-甲基噻吩)、聚[3,4-(伸乙基-1,2-二氧)噻吩](poly[3,4-(ethylene-1,2-dioxy)thiophene]，PEDOT)、聚吡咯及聚苯胺等，但不限於此。 As the first electrode material, a material with a high work function is generally preferred to facilitate the injection of holes into the organic material layer. Specific examples of the first electrode material that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) ) And indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO: Al or SnO 2 : Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4- (Ethylene-1,2-dioxy)thiophene] (poly[3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole, polyaniline, etc., but not limited thereto.
作為第二電極材料，通常較佳的是具有低的功函數的材料以有利於將電子注入有機材料層中。第二電極材料的具體實例包括：金屬，例如鎂、鈣、鈉、鉀、鈦、銦、釔、鋰、釓、鋁、銀、錫及鉛，或其合金；多層式結構材料，例如LiF/Al或LiO2/Al等，但不限於此。 As the second electrode material, a material with a low work function is generally preferred to facilitate the injection of electrons into the organic material layer. Specific examples of the second electrode material include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gamma, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials, such as LiF/ Al or LiO 2 /Al, etc., but not limited to this.
所述電洞注入層是自電極注入電洞的層，且電洞注入材料較佳為以下化合物，所述化合物具有傳輸電洞的能力，且因此具有於第一電極處注入電洞的效果以及將電洞注入發光層或發光材料的優異效果，防止自發光層所產生的激子移動至電子注入層或電子注入材料，且在形成薄膜能力方面亦為優異的。電洞注入材料的最高佔用分子軌域(highest occupied molecular orbital，HOMO)較佳為處於第一電極材料的功函數與相鄰的有機材料層的最高佔用分子軌域之間的值。電洞注入材料的具體實例包括金屬卟啉、寡聚噻吩、芳基胺系有機材料、六腈六氮雜苯并菲系有機材料、喹吖啶酮系有機材料、苝系有機材料、蒽醌、聚苯胺系導電聚合物及聚噻吩系導電聚合物等，但不限於此。 The hole injection layer is a layer in which holes are injected from the electrode, and the hole injection material is preferably the following compound, which has the ability to transport holes and therefore has the effect of injecting holes at the first electrode and The excellent effect of injecting holes into the light-emitting layer or the light-emitting material prevents excitons generated from the light-emitting layer from moving to the electron injection layer or the electron injection material, and is also excellent in the ability to form a thin film. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the first electrode material and the highest occupied molecular orbital of the adjacent organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone , Polyaniline-based conductive polymers and polythiophene-based conductive polymers, etc., but not limited to these.
所述電洞傳輸層為自電洞注入層接受電洞並將電洞傳輸 至發光層的層，且電洞傳輸材料合適地為可自第一電極或電洞注入層接受電洞並將電洞轉移至發光層的具有高電洞遷移率(mobility)的材料。其具體實例包括芳基胺系有機材料、導電聚合物、具有共軛部分及非共軛部分二者的嵌段共聚物(block copolymer)等，但不限於此。 The hole transmission layer accepts holes from the hole injection layer and transmits the holes The layer to the light-emitting layer, and the hole transport material is suitably a material with high hole mobility that can accept holes from the first electrode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, and the like, but are not limited thereto.
可在電洞傳輸層與發光層之間設置電子阻擋層。對於電子阻擋層，可使用此項技術中已知的材料。 An electron blocking layer can be provided between the hole transport layer and the light emitting layer. For the electron blocking layer, materials known in the art can be used.
發光層可包含主體材料及摻雜劑材料。主體材料包括本申請案的式1的化合物，且可更包括其他稠芳族環衍生物或含雜環化合物。具體而言，稠芳族環衍生物的實例包括蒽衍生物、芘衍生物、萘衍生物、稠五苯衍生物、菲化合物、螢蒽化合物等，且含雜環化合物的實例包括咔唑衍生物、二苯并呋喃、二苯并呋喃衍生物、二苯并噻吩、二苯并噻吩衍生物、梯型(ladder-type)呋喃化合物、嘧啶衍生物等，但其實例不限於此。
The light-emitting layer may include a host material and a dopant material. The host material includes the compound of
摻雜劑材料的實例包括下述化合物，但不限於此。 Examples of dopant materials include the following compounds, but are not limited thereto.
電子傳輸層為接受來自電子注入層的電子並將電子傳輸至發光層的層，且電子傳輸材料合適地為具有高電子遷移率的材料，其可熟練地接受來自第二電極的電子並將電子轉移至發光層。其具體實例包括：8-羥基喹啉的Al錯合物；包含Alq3的錯合物；有機自由基化合物；羥基黃酮-金屬錯合物(hydroxyflavone-metal complex)等，但不限於此。所述電子傳輸層可與任何所需陰極材料一起使用，如根據先前技術所用。具體而言，合宜的陰極材料的實例包括具有低功函數的典型材料，隨 後是鋁層或銀層。其具體實例包括銫、鋇、鈣、鐿及釤，在每一種情況下皆隨後是鋁層或銀層。 The electron transport layer is a layer that accepts electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material with high electron mobility, which can skillfully accept electrons from the second electrode and transfer electrons to the light emitting layer. Transfer to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. Specifically, examples of suitable cathode materials include typical materials with a low work function. After that is the aluminum layer or the silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, followed by an aluminum layer or a silver layer in each case.
電子注入層是自電極注入電子的層，且電極注入材料較佳為以下化合物，所述化合物具有傳輸電子的能力，具有自第二電極注入電子的效果以及將電子注入發光層或發光材料的優異效果，防止自發光層所產生的激子移動至電洞注入層，且在形成薄膜能力方面亦為優異的。其具體實例包括芴酮、蒽醌二甲烷、聯苯醌、噻喃二氧化物(thiopyran dioxide)、噁唑、噁二唑、***、咪唑、苝四羧酸、亞芴基甲烷(fluorenylidene methane)、蒽酮等及其衍生物、金屬錯合化合物、含氮的5員環衍生物等，但不限於此。 The electron injection layer is a layer that injects electrons from the electrode, and the electrode injection material is preferably the following compound, which has the ability to transport electrons, has the effect of injecting electrons from the second electrode, and is excellent in injecting electrons into the light-emitting layer or the light-emitting material The effect is to prevent excitons generated from the light-emitting layer from moving to the hole injection layer, and it is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane ), anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.
所述金屬錯合化合物的實例包括8-羥基喹啉鋰、雙(8-羥基喹啉)鋅、雙(8-羥基喹啉)銅、雙(8-羥基喹啉)錳、三(8-羥基喹啉)鋁、三(2-甲基-8-羥基喹啉)鋁、三(8-羥基喹啉)鎵、雙(10-羥基苯并[h]喹啉)鈹、雙(10-羥基苯并[h]喹啉)鋅、雙(2-甲基-8-喹啉)氯鎵、雙(2-甲基-8-喹啉)(鄰甲酚)鎵、雙(2-甲基-8-喹啉)(1-萘酚)鋁、雙(2-甲基-8-喹啉)(2-萘酚)鎵等，但不限於此。 Examples of the metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) Hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo(h)quinoline) beryllium, bis(10- Hydroxybenzo(h)quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline) (o-cresol) gallium, bis(2-methyl) Base-8-quinoline) (1-naphthol) aluminum, bis(2-methyl-8-quinoline) (2-naphthol) gallium, etc., but not limited thereto.
電洞阻擋層為阻擋電洞到達第二電極的層且通常可在與電洞注入層的條件相同的條件下形成。其具體實例包括噁二唑衍生物或***衍生物、啡啉衍生物、浴銅靈(bathocuproine，BCP)、鋁錯合物等，但不限於此。 The hole blocking layer is a layer that blocks holes from reaching the second electrode and can generally be formed under the same conditions as the hole injection layer. Specific examples thereof include oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, bathocuproine (BCP), aluminum complexes, etc., but are not limited thereto.
根據本說明書的有機發光元件根據待使用的材料可為頂 部發射型、底部發射型或雙發射型。 The organic light-emitting element according to this specification can be topped according to the material to be used. Part launch type, bottom launch type or dual launch type.
[本發明的方式] [Mode of the present invention]
以下，將藉由實例更詳細地闡述本說明書。然而，以下實例僅是為例示本說明書而提供，而不旨在限制本說明書。 Hereinafter, this specification will be explained in more detail with examples. However, the following examples are only provided to illustrate this specification, and are not intended to limit this specification.
根據本說明書的化合物使用布赫瓦爾德-哈特威格偶合反應(Buchwald-Hartwig coupling reaction)、赫克偶合反應(Heck coupling reaction)、鈴木偶合反應(Suzuki coupling reaction)等作為代表性反應來製備。 The compounds according to this specification are prepared using Buchwald-Hartwig coupling reaction, Heck coupling reaction, Suzuki coupling reaction, etc. as representative reactions .
[製備例1]製備式a(5H-苯并[b]咔唑) [Preparation Example 1] Preparation formula a (5H-benzo[b]carbazole)
1)製備式a-1 1) Preparation formula a-1
將300.0克(1.0當量)萘-2-胺、592.7克(1.0當量)1-溴-2-碘苯、302.0克(1.5當量)NaOtBu、4.70克(0.01當量)乙酸鈀(Pd(OAc)2)及12.12克(0.01當量)4,5-雙(二苯基膦基)-9,9-二甲基呫噸(Xantphos)溶解在5升1,4-二噁烷中，且在回流下對所得溶液進行了攪拌。當反應在3小時後終止時，藉由減壓移除了溶劑。此後，將所得產物完全溶解在乙酸乙酯中，用水對所得溶液進行了洗滌，且藉由減壓再次移除約70%的溶劑。再次，在回流狀態下向其中添加己烷的同時沈澱了晶體，冷卻，然後過濾。 對所得產物進行了管柱層析，以獲得443.5克(產率71%)化合物a-1。[M+H]=299 300.0 g (1.0 equivalent) naphthalene-2-amine, 592.7 g (1.0 equivalent) 1-bromo-2-iodobenzene, 302.0 g (1.5 equivalent) NaOtBu, 4.70 g (0.01 equivalent) palladium acetate (Pd(OAc) 2 ) And 12.12 grams (0.01 equivalent) 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) dissolved in 5 liters of 1,4-dioxane and under reflux The resulting solution was stirred. When the reaction was terminated after 3 hours, the solvent was removed by reduced pressure. After that, the resultant product was completely dissolved in ethyl acetate, the resultant solution was washed with water, and about 70% of the solvent was removed again by reducing pressure. Again, crystals were precipitated while adding hexane to it under reflux, cooled, and then filtered. The resulting product was subjected to column chromatography to obtain 443.5 g (yield 71%) of compound a-1. [M+H]=299
2)製備式a(5H-苯并[b]咔唑) 2) Preparation formula a (5H-benzo[b]carbazole)
將443.5克(1.0當量)式a-1、8.56克(0.01當量)Pd(t-Bu3P)2及463.2克(2.00當量)K2CO3放入4升二甲基乙醯胺(dimethylacetamide，DMAC)中，且在回流下對所得混合物進行了攪拌。3小時後，藉由將反應物倒入水中對晶體進行了沈澱，並過濾。在過濾的固體完全溶解在1,2-二氯苯中後，用水對所得溶液進行了洗滌，藉由在減壓下濃縮溶解有產物的溶液對晶體進行了沈澱，冷卻，然後過濾。藉由管柱層析對所得產物進行了純化，以獲得174.8克(產率48%)式a(5H-苯并[b]咔唑)。[M+H]=218 Put 443.5 grams (1.0 equivalent) of formula a-1, 8.56 grams (0.01 equivalent) Pd(t-Bu 3 P) 2 and 463.2 grams (2.00 equivalent) K 2 CO 3 into 4 liters of dimethylacetamide , DMAC), and the resulting mixture was stirred under reflux. After 3 hours, the crystals were precipitated by pouring the reactant into water and filtered. After the filtered solid was completely dissolved in 1,2-dichlorobenzene, the resulting solution was washed with water, and the crystals were precipitated by concentrating the solution in which the product was dissolved under reduced pressure, cooling, and then filtering. The resulting product was purified by column chromatography to obtain 174.8 g (yield 48%) of formula a (5H-benzo[b]carbazole). [M+H]=218
此處，tBu意指第三丁基。 Here, tBu means tertiary butyl group.
[製備例2]製備式b(7H-二苯并[b,g]咔唑) [Preparation Example 2] Preparation formula b (7H-dibenzo[b,g]carbazole)
藉由使用1-溴-2-碘萘代替1-溴-2-碘苯，以與製備式a的方法相同的方式合成了式b(7H-二苯并[b,g]咔唑)。 By using 1-bromo-2-iodonaphthalene instead of 1-bromo-2-iodobenzene, formula b (7H-dibenzo[b,g]carbazole) was synthesized in the same manner as the method for preparing formula a.
[製備例3]製備式c(6H-二苯并[b,h]咔唑) [Preparation Example 3] Preparation formula c (6H-dibenzo[b,h]carbazole)
藉由使用2,3-二溴萘代替1-溴-2-碘苯，以與製備式a的 方法相同的方式合成了式c(6H-二苯并[b,h]咔唑)。 By using 2,3-dibromonaphthalene instead of 1-bromo-2-iodobenzene, it can be compared with the preparation of formula a The formula c (6H-dibenzo[b,h]carbazole) was synthesized in the same way.
[製備例4]製備式d(13H-二苯并[a,h]咔唑) [Preparation Example 4] Preparation formula d (13H-dibenzo[a,h]carbazole)
藉由使用2-溴-1-碘萘代替1-溴-2-碘苯，以與製備式a的方法相同的方式合成了式b(13H-二苯并[a,h]咔唑)。 By using 2-bromo-1-iodonaphthalene instead of 1-bromo-2-iodobenzene, formula b (13H-dibenzo[a,h]carbazole) was synthesized in the same manner as the method for preparing formula a.
[製備例5]製備式e [Preparation Example 5] Preparation formula e
1)製備式e-2 1) Preparative formula e-2
將200.0克(1.0當量)1-溴-4-氯-3-氟-2-碘苯、82.3克(1.0當量)(2-羥基苯基)硼酸、164.6克(2.0當量)K2CO3及13.77克(0.02當量)Pd(PPh3)4(四(三苯基膦)鈀(0))溶解在3升四氫呋 喃(tetrahydrofuran，THF)中，且在回流下對所得溶液進行了攪拌。當反應在2小時後終止時，藉由減壓移除了溶劑。此後，將所得產物完全溶解在乙酸乙酯中並用水洗滌，且藉由減壓再次移除了約80%的溶劑。再次，在回流狀態下向其中添加己烷的同時沈澱了晶體，冷卻，然後過濾。對所得產物進行了管柱層析，以獲得129.5克(產率72%)化合物e-2。[M+H]+=300 200.0 g (1.0 equivalent) 1-bromo-4-chloro-3-fluoro-2-iodobenzene, 82.3 g (1.0 equivalent) (2-hydroxyphenyl)boronic acid, 164.6 g (2.0 equivalent) K 2 CO 3 and 13.77 g (0.02 equivalent) of Pd(PPh 3 ) 4 (tetra(triphenylphosphine)palladium(0)) was dissolved in 3 liters of tetrahydrofuran (THF), and the resulting solution was stirred under reflux. When the reaction was terminated after 2 hours, the solvent was removed by reducing pressure. After that, the resulting product was completely dissolved in ethyl acetate and washed with water, and about 80% of the solvent was removed again by reducing pressure. Again, crystals were precipitated while adding hexane to it under reflux, cooled, and then filtered. The resulting product was subjected to column chromatography to obtain 129.5 g (yield 72%) of compound e-2. [M+H]+=300
2)製備式e-1 2) Preparation formula e-1
將129.5克(1.0當量)式a-2及118.5克(2.00當量)K2CO3放入2升二甲基乙醯胺中，且在回流下對所得混合物進行了攪拌。1小時後，藉由將反應物倒入水中對晶體進行了沈澱，並過濾。將過濾的固體完全溶解在乙酸乙酯中並用水洗滌，且藉由減壓再次移除了約70%的溶劑。再次，在回流狀態下向其中放入己烷，且沈澱了晶體，冷卻，然後過濾。對所得產物進行了管柱層析，以獲得101.6克(產率84%)化合物e-1。[M+H]+=280 129.5 g (1.0 equivalent) of formula a-2 and 118.5 g (2.00 equivalent) of K 2 CO 3 were put into 2 liters of dimethylacetamide, and the resulting mixture was stirred under reflux. After 1 hour, the crystals were precipitated by pouring the reactant into water and filtered. The filtered solid was completely dissolved in ethyl acetate and washed with water, and about 70% of the solvent was removed again by reducing pressure. Again, hexane was put into it under reflux, and crystals were precipitated, cooled, and then filtered. The resulting product was subjected to column chromatography to obtain 101.6 g (yield 84%) of compound e-1. [M+H]+=280
3)製備式e 3) Preparative formula e
將101.6克(1.0當量)式e-1、119.1克(1.3當量)雙(頻哪醇基)二硼、5.28克(0.02當量)(1,1'-雙(二苯基膦基)二茂鐵)二氯化鈀(Pd(dppf)Cl2)及40.4克(2.00當量)乙酸鉀(KOAc)放入2升二噁烷中，且在回流下對所得混合物進行了攪拌。當反應在3小時後終止時，藉由減壓移除了溶劑。將過濾的固體完全溶解在CHCl3中，然後用水洗滌，且藉由在減壓下濃縮溶解有產物的溶液來移除約90%的溶劑。在回流狀態下向其中添加乙醇的 同時沈澱了晶體，冷卻，然後過濾以獲得103.1克(產率87%)式e。[M+H]+=329 101.6 g (1.0 equivalent) formula e-1, 119.1 g (1.3 equivalent) bis(pinacol) diboron, 5.28 g (0.02 equivalent) (1,1'-bis(diphenylphosphino) dicene Iron) palladium dichloride (Pd(dppf)Cl 2 ) and 40.4 g (2.00 equivalents) of potassium acetate (KOAc) were put in 2 liters of dioxane, and the resulting mixture was stirred under reflux. When the reaction was terminated after 3 hours, the solvent was removed by reduced pressure. The filtered solid was completely dissolved in CHCl 3 and then washed with water, and about 90% of the solvent was removed by concentrating the solution in which the product was dissolved under reduced pressure. Crystals were precipitated while adding ethanol to it under reflux, cooled, and then filtered to obtain 103.1 g (yield 87%) of formula e. [M+H]+=329
[製備例6]製備式f [Preparation Example 6] Preparation formula f
藉由使用1-溴-5-氯-3-氟-2-碘苯代替1-溴-4-氯-3-氟-2-碘苯，以與製備式e的方法相同的方式合成了下式f。[M+H]+=329 By using 1-bromo-5-chloro-3-fluoro-2-iodobenzene instead of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, the following was synthesized in the same manner as the method for preparing formula e式f. [M+H]+=329
[製備例7]製備式g [Preparation Example 7] Preparation formula g
藉由使用2-溴-1-氯-4-氟-3-碘苯代替1-溴-4-氯-3-氟-2-碘苯，以與製備式e的方法相同的方式合成了下式g。[M+H]+=329 By using 2-bromo-1-chloro-4-fluoro-3-iodobenzene instead of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, the following was synthesized in the same manner as the method for preparing formula e式g。 Formula g. [M+H]+=329
[製備例8]製備式h [Preparation Example 8] Preparation formula h
藉由使用(3-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式e的方法相同的方式合成了下式h。[M+H]+=379 By using (3-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following formula h was synthesized in the same manner as the method for preparing formula e. [M+H]+=379
[製備例9]製備式i [Preparation Example 9] Preparation formula i
藉由使用(3-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式f的方法相同的方式合成了下式i。[M+H]+=379 By using (3-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following formula i was synthesized in the same manner as the method for preparing formula f. [M+H]+=379
[製備例10]製備式j [Preparation Example 10] Preparation formula j
藉由使用(3-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式f的方法相同的方式合成了下式j。[M+H]+=379 By using (3-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following formula j was synthesized in the same manner as the method for preparing formula f. [M+H]+=379
[製備例11]製備k [Preparation Example 11] Preparation k
藉由使用(1-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式e的方法相同的方式合成了下式k。[M+H]+=379 By using (1-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following formula k was synthesized in the same manner as the method for preparing formula e. [M+H]+=379
[製備例12]製備式l
[Preparation Example 12]
藉由使用(1-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式f的方法相同的方式合成了下式l。[M+H]+=379
By using (1-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following
[製備例13]製備式m [Preparation Example 13] Preparation formula m
藉由使用(1-羥基萘-2-基)硼酸代替(2-羥基苯基)硼酸，以與製備式g的方法相同的方式合成了下式m。[M+H]+=379 By using (1-hydroxynaphthalene-2-yl)boronic acid instead of (2-hydroxyphenyl)boronic acid, the following formula m was synthesized in the same manner as the method for preparing formula g. [M+H]+=379
[製備例14]製備式n [Preparation Example 14] Preparation formula n
藉由使用2-溴-1-氯-4-氟-3-碘萘代替1-溴-4-氯-3-氟-2-碘苯，以與製備式e的方法相同的方式合成了下式n。[M+H]+=379 By using 2-bromo-1-chloro-4-fluoro-3-iodonaphthalene instead of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, the following was synthesized in the same manner as the method for preparing formula e式n。 Formula n. [M+H]+=379
[製備例15]製備式o [Preparation Example 15] Preparation formula o
藉由使用1-溴-4-氯-3-氟-2-碘萘代替1-溴-4-氯-3-氟-2-碘苯，以與製備式e的方法相同的方式合成了下式o。[M+H]+=379 By using 1-bromo-4-chloro-3-fluoro-2-iodonaphthalene instead of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, the following was synthesized in the same manner as the method for preparing formula e式 o. [M+H]+=379
藉由利用在製備例1至製備例15中合成的中間物，使包 括三嗪在內的中間物進行鈴木偶合反應，且合成了以下合成例中的化合物。 By using the intermediates synthesized in Preparation Example 1 to Preparation Example 15, the package Intermediates including triazines were subjected to Suzuki coupling reaction, and the compounds in the following synthesis examples were synthesized.
[合成例1] [Synthesis Example 1]
在氮氣氣氛下，將中間物1(10克，20.7毫莫耳)及式a(4.5克，20.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(NaOtBu)(6克，62毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(Pd(t-Bu3P)2)(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物1(8.2克，60%，質譜分析(mass spectrum，MS)：[M+H]+=665.8)。
Under a nitrogen atmosphere, intermediate 1 (10 g, 20.7 millimoles) and formula a (4.5 g, 20.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (NaOtBu) (6 g, 62 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (Pd(t- Bu 3 P) 2 ) (0.2 g, 0.4 millimolar). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare
[合成例2] [Synthesis Example 2]
在氮氣氣氛下，將中間物2(10克，23毫莫耳)及式a(5克，23毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6.6克，69.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.5毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物2(9.9克，70%，MS：[M+H]+=615.2)。 Under a nitrogen atmosphere, intermediate 2 (10 g, 23 millimoles) and formula a (5 g, 23 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6.6 g, 69.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.5 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 2 (9.9 g, 70%, MS: [M+H]+=615.2) as a yellow solid compound.
[合成例3] [Synthesis Example 3]
在氮氣氣氛下，將中間物3(10克，19.1毫莫耳)及式a(4.1克，19.1毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.5克，57.3毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物3(9.3克，69%，MS：[M+H]+=705.2)。 Under a nitrogen atmosphere, intermediate 3 (10 g, 19.1 millimoles) and formula a (4.1 g, 19.1 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.5 g, 57.3 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 3 (9.3 g, 69%, MS: [M+H]+=705.2) as a yellow solid compound.
[合成例4] [Synthesis Example 4]
在氮氣氣氛下，將中間物4(10克，15.9毫莫耳)及式a(3.4克，15.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.6克，47.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物4(8.7克，68%，MS：[M+H]+=811.2)。 Under a nitrogen atmosphere, intermediate 4 (10 g, 15.9 mmol) and formula a (3.4 g, 15.9 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.6 g, 47.6 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 4 (8.7 g, 68%, MS: [M+H]+=811.2) as a yellow solid compound.
[合成例5] [Synthesis Example 5]
在氮氣氣氛下，將中間物5(10克，23毫莫耳)及式a(5克，23毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6.6克，69.1 毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.5毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物5(8.5克，60%，MS：[M+H]+=615.2)。 Under a nitrogen atmosphere, intermediate 5 (10 g, 23 millimoles) and formula a (5 g, 23 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6.6 g, 69.1 Millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.5 millimoles) was introduced into it. After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 5 (8.5 g, 60%, MS: [M+H]+=615.2) as a yellow solid compound.
[合成例6] [Synthesis Example 6]
在氮氣氣氛下，將中間物6(10克，17.9毫莫耳)及式a(3.9克，17.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.1克，53.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層 進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物6(8.3克，63%，MS：[M+H]+=741.3)。 Under a nitrogen atmosphere, intermediate 6 (10 g, 17.9 mmol) and formula a (3.9 g, 17.9 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.1 g, 53.6 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer Distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 6 (8.3 g, 63%, MS: [M+H]+=741.3) as a yellow solid compound.
[合成例7] [Synthesis Example 7]
在氮氣氣氛下，將中間物7(10克，18.5毫莫耳)及式a(4克，18.5毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.3克，55.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了 蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物7(8.7克，65%，MS：[M+H]+=721.2)。 Under a nitrogen atmosphere, intermediate 7 (10 g, 18.5 millimoles) and formula a (4 g, 18.5 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.3 g, 55.6 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was carried out Distillation. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 7 (8.7 g, 65%, MS: [M+H]+=721.2) as a yellow solid compound.
[合成例8] [Synthesis Example 8]
在氮氣氣氛下，將中間物8(10克，16.7毫莫耳)及式a(3.6克，16.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.8克，50.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物8(8.2克，63%，MS：[M+H]+=780.3)。 Under a nitrogen atmosphere, intermediate 8 (10 g, 16.7 millimoles) and formula a (3.6 g, 16.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.8 g, 50.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 8 (8.2 g, 63%, MS: [M+H]+=780.3) as a yellow solid compound.
[合成例9] [Synthesis Example 9]
在氮氣氣氛下，將中間物9(10克，23毫莫耳)及式a(5克，23毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6.6克，69.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.5毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物9(9.1克，64%，MS：[M+H]+=615.2)。 Under a nitrogen atmosphere, intermediate 9 (10 g, 23 millimoles) and formula a (5 g, 23 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6.6 g, 69.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.5 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 9 (9.1 g, 64%, MS: [M+H]+=615.2) as a yellow solid compound.
[合成例10] [Synthesis Example 10]
在氮氣氣氛下，將中間物10(10克，18.7毫莫耳)及式a(4.1克，18.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.4克，56.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物10(7.9克，59%，MS：[M+H]+=715.2)。 Under a nitrogen atmosphere, intermediate 10 (10 g, 18.7 millimoles) and formula a (4.1 g, 18.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.4 g, 56.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 10 (7.9 g, 59%, MS: [M+H]+=715.2) as a yellow solid compound.
[合成例11] [Synthesis Example 11]
在氮氣氣氛下，將中間物11(10克，18.7毫莫耳)及式a(4.1克，18.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.4克，56.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物11(8.6克，64%，MS：[M+H]+=715.2)。 Under a nitrogen atmosphere, intermediate 11 (10 g, 18.7 millimoles) and formula a (4.1 g, 18.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.4 g, 56.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 11 (8.6 g, 64%, MS: [M+H]+=715.2) as a yellow solid compound.
[合成例12] [Synthesis Example 12]
在氮氣氣氛下，將中間物12(10克，16.3毫莫耳)及式a(3.5克，16.3毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.7克， 48.9毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中放入了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物12(8.9克，69%，MS：[M+H]+=795.2)。 Under a nitrogen atmosphere, intermediate 12 (10 g, 16.3 millimoles) and formula a (3.5 g, 16.3 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.7 g, 48.9 millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.3 millimoles) was introduced into it. After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was put therein, the resulting mixture was stirred, then filtered, and under reduced pressure The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 12 (8.9 g, 69%, MS: [M+H]+=795.2) as a yellow solid compound.
[合成例13] [Synthesis Example 13]
在氮氣氣氛下，將中間物13(10克，16.7毫莫耳)及式a(3.6克，16.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.8克，50.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水 將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物13(8.6克，66%，MS：[M+H]+=780.3)。 Under a nitrogen atmosphere, intermediate 13 (10 g, 16.7 millimoles) and formula a (3.6 g, 16.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.8 g, 50.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. Introduce the distilled organic layer into chloroform again and dissolve it with water The solution was washed twice, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 13 (8.6 g, 66%, MS: [M+H]+=780.3) as a yellow solid compound.
[合成例14] [Synthesis Example 14]
在氮氣氣氛下，將中間物14(10克，20.7毫莫耳)及式a(4.5克，20.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6克，62毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進 行了純化以製備為黃色固體化合物的化合物14(9.1克，66%，MS：[M+H]+=665.2)。 Under a nitrogen atmosphere, intermediate 14 (10 g, 20.7 millimoles) and formula a (4.5 g, 20.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6 g, 62 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. Use chloroform and ethyl acetate to analyze the concentrated compound through a silica column. Purification was performed to prepare compound 14 (9.1 g, 66%, MS: [M+H]+=665.2) as a yellow solid compound.
[合成例15] [Synthesis Example 15]
在氮氣氣氛下，將中間物15(10克，16.9毫莫耳)及式a(3.7克，16.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.9克，50.8毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物15(8.4克，64%，MS：[M+H]+=771.2)。 Under a nitrogen atmosphere, intermediate 15 (10 g, 16.9 mmol) and formula a (3.7 g, 16.9 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.9 g, 50.8 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 15 (8.4 g, 64%, MS: [M+H]+=771.2) as a yellow solid compound.
[合成例16] [Synthesis Example 16]
在氮氣氣氛下，將中間物16(10克，18.7毫莫耳)及式a(4.1克，18.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.4克，56.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物16(7.8克，58%，MS：[M+H]+=715.2)。 Under a nitrogen atmosphere, intermediate 16 (10 g, 18.7 millimoles) and formula a (4.1 g, 18.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.4 g, 56.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 16 (7.8 g, 58%, MS: [M+H]+=715.2) as a yellow solid compound.
[合成例17] [Synthesis Example 17]
在氮氣氣氛下，將中間物17(10克，15.7毫莫耳)及式a(3.4克，15.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.5克，47.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物17(7.6克，59%，MS：[M+H]+=817.3)。 Under a nitrogen atmosphere, intermediate 17 (10 g, 15.7 mmol) and formula a (3.4 g, 15.7 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.5 g, 47.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 17 (7.6 g, 59%, MS: [M+H]+=817.3) as a yellow solid compound.
[合成例18] [Synthesis Example 18]
在氮氣氣氛下，將中間物18(10克，20.7毫莫耳)及式a(4.5克，20.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6克，62毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物18(7.8克，57%，MS：[M+H]+=665.2)。 Under a nitrogen atmosphere, intermediate 18 (10 g, 20.7 millimoles) and formula a (4.5 g, 20.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6 g, 62 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 18 (7.8 g, 57%, MS: [M+H]+=665.2) as a yellow solid compound.
[合成例19] [Synthesis Example 19]
在氮氣氣氛下，將中間物19(10克，18.7毫莫耳)及式a(4.1克，18.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.4克， 56.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物19(8.7克，65%，MS：[M+H]+=715.2)。 Under a nitrogen atmosphere, intermediate 19 (10 g, 18.7 millimoles) and formula a (4.1 g, 18.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.4 g, 56.2 millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.4 millimoles) was introduced into it. After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 19 (8.7 g, 65%, MS: [M+H]+=715.2) as a yellow solid compound.
[合成例20] [Synthesis Example 20]
在氮氣氣氛下，將中間物20(10克，15.4毫莫耳)及式a(3.3克，15.4毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.4克，46.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有 機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物20(7.7克，60%，MS：[M+H]+=831.3)。 Under a nitrogen atmosphere, intermediate 20 (10 g, 15.4 mmol) and formula a (3.3 g, 15.4 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.4 g, 46.1 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 mmol) was introduced into it. ). After reacting for 2 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer. The machine layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 20 (7.7 g, 60%, MS: [M+H]+=831.3) as a yellow solid compound.
[合成例21] [Synthesis Example 21]
在氮氣氣氛下，將中間物21(10克，15.7毫莫耳)及式a(3.4克，15.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.5克，47.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進 行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物21(7.3克，57%，MS：[M+H]+=817.3)。 Under a nitrogen atmosphere, intermediate 21 (10 g, 15.7 millimoles) and formula a (3.4 g, 15.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.5 g, 47.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and Filtrate into Distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 21 (7.3 g, 57%, MS: [M+H]+=817.3) as a yellow solid compound.
[合成例22] [Synthesis Example 22]
在氮氣氣氛下，將中間物22(10克，15.6毫莫耳)及式a(3.4克，15.6毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.5克，46.9毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物22(8.2克，64%，MS：[M+H]+=821.2)。 Under a nitrogen atmosphere, the intermediate 22 (10 g, 15.6 millimoles) and formula a (3.4 g, 15.6 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.5 g, 46.9 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 mmol) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 22 (8.2 g, 64%, MS: [M+H]+=821.2) as a yellow solid compound.
[合成例23] [Synthesis Example 23]
在氮氣氣氛下，將中間物23(10克，17.9毫莫耳)及式b(4.8克，17.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.1克，53.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物23(7.8克，55%，MS：[M+H]+=791.3)。 Under a nitrogen atmosphere, intermediate 23 (10 g, 17.9 mmol) and formula b (4.8 g, 17.9 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.1 g, 53.6 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 23 (7.8 g, 55%, MS: [M+H]+=791.3) as a yellow solid compound.
[合成例24] [Synthesis Example 24]
在氮氣氣氛下，將中間物24(10克，17.1毫莫耳)及式b(4.6克，17.1毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.9克，51.4毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物24(8.8克，63%，MS：[M+H]+=815.3)。 Under a nitrogen atmosphere, intermediate 24 (10 g, 17.1 mmol) and formula b (4.6 g, 17.1 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.9 g, 51.4 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 mmol) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 24 (8.8 g, 63%, MS: [M+H]+=815.3) as a yellow solid compound.
[合成例25] [Synthesis Example 25]
在氮氣氣氛下，將中間物25(10克，15.4毫莫耳)及式b(4.1克，15.4毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.4克，46.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物25(7.6克，56%，MS：[M+H]+=880.3)。 Under a nitrogen atmosphere, intermediate 25 (10 g, 15.4 mmol) and formula b (4.1 g, 15.4 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.4 g, 46.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 25 (7.6 g, 56%, MS: [M+H]+=880.3) as a yellow solid compound.
[合成例26] [Synthesis Example 26]
在氮氣氣氛下，將中間物26(10克，19.6毫莫耳)及式b(5.2克，19.6毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.7克， 58.8毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物26(9.4克，65%，MS：[M+H]+=741.3)。 Under a nitrogen atmosphere, intermediate 26 (10 g, 19.6 mmol) and formula b (5.2 g, 19.6 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.7 g, 58.8 millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.4 millimoles) was introduced into it. After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 26 (9.4 g, 65%, MS: [M+H]+=741.3) as a yellow solid compound.
[合成例27] [Synthesis Example 27]
在氮氣氣氛下，將中間物27(10克，16.3毫莫耳)及式b(4.4克，16.3毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.7克，48.9毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有 機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物27(8.5克，62%，MS：[M+H]+=845.3)。 Under a nitrogen atmosphere, intermediate 27 (10 g, 16.3 mmol) and formula b (4.4 g, 16.3 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.7 g, 48.9 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 mmol) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer. The machine layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 27 (8.5 g, 62%, MS: [M+H]+=845.3) as a yellow solid compound.
[合成例28] [Synthesis Example 28]
在氮氣氣氛下，將中間物28(10克，14.3毫莫耳)及式b(3.8克，14.3毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.1克，42.9毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.1克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進 行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物28(7.3克，55%，MS：[M+H]+=930.3)。 Under a nitrogen atmosphere, intermediate 28 (10 g, 14.3 mmol) and formula b (3.8 g, 14.3 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.1 g, 42.9 mmol) was introduced into it, the resulting mixture was sufficiently stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.1 g, 0.3 mmol) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and Filtrate into Distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 28 (7.3 g, 55%, MS: [M+H]+=930.3) as a yellow solid compound.
[合成例29] [Synthesis Example 29]
在氮氣氣氛下，將中間物29(10克，23毫莫耳)及式c(6.2克，23毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6.6克，69.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.5毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物29(9克，59%，MS：[M+H]+=665.2)。 Under a nitrogen atmosphere, intermediate 29 (10 g, 23 millimoles) and formula c (6.2 g, 23 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6.6 g, 69.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.5 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 29 (9 g, 59%, MS: [M+H]+=665.2) as a yellow solid compound.
[合成例30] [Synthesis Example 30]
在氮氣氣氛下，將中間物30(10克，20.7毫莫耳)及式c(5.5克，20.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6克，62毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物30(10.2克，69%，MS：[M+H]+=715.2)。 Under a nitrogen atmosphere, intermediate 30 (10 g, 20.7 millimoles) and formula c (5.5 g, 20.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6 g, 62 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 30 (10.2 g, 69%, MS: [M+H]+=715.2) as a yellow solid compound.
[合成例31] [Synthesis Example 31]
在氮氣氣氛下，將中間物31(10克，17.9毫莫耳)及式c(4.8克，17.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.1克，53.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物31(8克，57%，MS：[M+H]+=791.3)。 Under a nitrogen atmosphere, intermediate 31 (10 g, 17.9 mmol) and formula c (4.8 g, 17.9 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.1 g, 53.6 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 31 (8 g, 57%, MS: [M+H]+=791.3) as a yellow solid compound.
[合成例32] [Synthesis Example 32]
在氮氣氣氛下，將中間物32(10克，17.4毫莫耳)及式c(4.7克，17.4毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5克，52.3毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物32(8克，57%，MS：[M+H]+=805.2)。 Under a nitrogen atmosphere, intermediate 32 (10 g, 17.4 mmol) and formula c (4.7 g, 17.4 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5 g, 52.3 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 32 (8 g, 57%, MS: [M+H]+=805.2) as a yellow solid compound.
[合成例33] [Synthesis Example 33]
在氮氣氣氛下，將中間物33(10克，23毫莫耳)及式c(6.2克，23毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6.6克，69.1毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.5毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物33(10.4克，68%，MS：[M+H]+=665.2)。 Under a nitrogen atmosphere, intermediate 33 (10 g, 23 millimoles) and formula c (6.2 g, 23 millimoles) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (6.6 g, 69.1 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.5 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 33 (10.4 g, 68%, MS: [M+H]+=665.2) as a yellow solid compound.
[合成例34] [Synthesis Example 34]
在氮氣氣氛下，將中間物34(10克，17.9毫莫耳)及式c(4.8克，17.9毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.1克， 53.6毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物34(9克，64%，MS：[M+H]+=791.9)。 Under a nitrogen atmosphere, intermediate 34 (10 g, 17.9 mmol) and formula c (4.8 g, 17.9 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.1 g, 53.6 millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.4 millimoles) was introduced into it. After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 34 (9 g, 64%, MS: [M+H]+=791.9) as a yellow solid compound.
[合成例35] [Synthesis Example 35]
在氮氣氣氛下，將中間物35(10克，19.1毫莫耳)及式c(5.1克，19.1毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.5克，57.4毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水 將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物35(9.9克，69%，MS：[M+H]+=754.3)。 Under a nitrogen atmosphere, intermediate 35 (10 g, 19.1 mmol) and formula c (5.1 g, 19.1 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.5 g, 57.4 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.4 mmol) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. Introduce the distilled organic layer into chloroform again and dissolve it with water The solution was washed twice, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 35 (9.9 g, 69%, MS: [M+H]+=754.3) as a yellow solid compound.
[合成例36] [Synthesis Example 36]
在氮氣氣氛下，將中間物36(10克，19.1毫莫耳)及式d(5.1克，19.1毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.5克，57.4毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合 物進行了純化以製備為黃色固體化合物的化合物36(9.9克，69%，MS：[M+H]+=754.3)。 Under a nitrogen atmosphere, intermediate 36 (10 g, 19.1 mmol) and formula d (5.1 g, 19.1 mmol) were put into 200 ml of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5.5 g, 57.4 mmol) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 mmol) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. Use chloroform and ethyl acetate to condense the compound with silica column The product was purified to prepare compound 36 (9.9 g, 69%, MS: [M+H]+=754.3) as a yellow solid compound.
[合成例37] [Synthesis Example 37]
在氮氣氣氛下，將中間物37(10克，16.2毫莫耳)及式d(4.3克，16.2毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.7克，48.7毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物37(8.1克，59%，MS：[M+H]+=847.3)。 Under a nitrogen atmosphere, intermediate 37 (10 g, 16.2 mmol) and formula d (4.3 g, 16.2 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.7 g, 48.7 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 37 (8.1 g, 59%, MS: [M+H]+=847.3) as a yellow solid compound.
[合成例38] [Synthesis Example 38]
在氮氣氣氛下，將中間物38(10克，16.2毫莫耳)及式d(4.3克，16.2毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.7克，48.7毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物38(7.7克，56%，MS：[M+H]+=847.3)。 Under a nitrogen atmosphere, intermediate 38 (10 g, 16.2 mmol) and formula d (4.3 g, 16.2 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (4.7 g, 48.7 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 38 (7.7 g, 56%, MS: [M+H]+=847.3) as a yellow solid compound.
[合成例39] [Synthesis Example 39]
在氮氣氣氛下，將中間物39(10克，16.7毫莫耳)及式d(4.5克，16.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(4.8克，50.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物39(8克，58%，MS：[M+H]+=830.3)。 Under a nitrogen atmosphere, intermediate 39 (10 g, 16.7 millimoles) and formula d (4.5 g, 16.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (4.8 g, 50.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 39 (8 g, 58%, MS: [M+H]+=830.3) as a yellow solid compound.
[合成例40] [Synthesis Example 40]
在氮氣氣氛下，將中間物40(10克，20.7毫莫耳)及式a(4.5克，20.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(6克，62 毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的40(8.5克，62%，MS：[M+H]+=665.2)。 Under a nitrogen atmosphere, intermediate 40 (10 g, 20.7 millimoles) and formula a (4.5 g, 20.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (6 g, 62 Millimoles), the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.2 g, 0.4 millimoles) was introduced into it. After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare 40 (8.5 g, 62%, MS: [M+H]+=665.2) as a yellow solid compound.
[合成例41] [Synthesis Example 41]
在氮氣氣氛下，將中間物41(10克，17.4毫莫耳)及式a(3.8克，17.4毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5克，52.3毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.3毫莫耳)。反應3小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶 液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物41(8.3克，63%，MS：[M+H]+=755.2)。 Under a nitrogen atmosphere, intermediate 41 (10 g, 17.4 mmol) and formula a (3.8 g, 17.4 mmol) were put into 200 mL of xylene, and the resulting mixture was stirred and refluxed. Thereafter, sodium tertiary butoxide (5 g, 52.3 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiary butylphosphine) palladium (0.2 g, 0.3 millimoles) was introduced into it. ). After reacting for 3 hours, the resulting product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. Introduce the distilled organic layer into chloroform again and dissolve it, and dissolve it with water After washing the liquid twice, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 41 (8.3 g, 63%, MS: [M+H]+=755.2) as a yellow solid compound.
[合成例42] [Synthesis Example 42]
在氮氣氣氛下，將中間物42(10克，18.7毫莫耳)及式c(5克，18.7毫莫耳)放入200毫升二甲苯中，且對所得混合物進行了攪拌及回流。此後，向其中引入了第三丁醇鈉(5.4克，56.2毫莫耳)，充分攪拌了所得混合物，然後向其中引入了雙(三第三丁基膦)鈀(0.2克，0.4毫莫耳)。反應2小時後，將所得產物冷卻至室溫，然後藉由過濾有機層來移除鹽，然後對過濾的有機層進行了蒸餾。將蒸餾的有機層再次引入氯仿中並溶解，用水將溶液洗滌了兩次，然後分離了有機層，向其中添加了無水硫酸鎂，對所得混合物進行了攪拌，然後過濾，且在減壓下對濾液進行了蒸餾。使用氯仿及乙酸乙酯藉由二氧化矽管柱對濃縮的化合物進行了純化以製備為黃色固體化合物的化合物42(9.3克，65%， MS：[M+H]+=765.3)。 Under a nitrogen atmosphere, intermediate 42 (10 g, 18.7 millimoles) and formula c (5 g, 18.7 millimoles) were put into 200 milliliters of xylene, and the resulting mixture was stirred and refluxed. After that, sodium tertiary butoxide (5.4 g, 56.2 millimoles) was introduced into it, the resulting mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine) palladium (0.2 g, 0.4 millimoles) was introduced into it. ). After reacting for 2 hours, the resultant product was cooled to room temperature, and then the salt was removed by filtering the organic layer, and then the filtered organic layer was distilled. The distilled organic layer was again introduced into chloroform and dissolved, the solution was washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the resulting mixture was stirred, then filtered, and The filtrate was distilled. The concentrated compound was purified by silica column using chloroform and ethyl acetate to prepare compound 42 as a yellow solid compound (9.3 g, 65%, MS: [M+H]+=765.3).
[比較例1] [Comparative Example 1]
將薄薄地塗佈氧化銦錫(ITO)以具有1,000埃厚度的玻璃基板放入溶解有洗滌劑(detergent)的蒸餾水中，並進行超音波洗滌。在此種情況下，使用費希爾公司(Fischer Co.)製造的產品作為洗滌劑，並使用密理博公司(Millipore Co.)製造的濾器過濾兩次的蒸餾水作為所述蒸餾水。在將ITO洗滌30分鐘後，使用蒸餾水重複兩次超音波洗滌達10分鐘。使用蒸餾水進行的洗滌結束後，使用異丙醇、丙酮及甲醇溶劑進行超音波洗滌，且對所得產物進行了乾燥，然後將其傳輸至電漿洗滌機(plasma washing machine)。此外，使用氧電漿將基板清洗了5分鐘，然後傳輸至真空沈積機。 A glass substrate thinly coated with indium tin oxide (ITO) to have a thickness of 1,000 angstroms was placed in distilled water in which detergent was dissolved, and ultrasonic washing was performed. In this case, a product manufactured by Fischer Co. is used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. is used as the distilled water. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes. After the washing with distilled water is completed, ultrasonic washing is performed with isopropanol, acetone, and methanol solvents, and the resultant product is dried, and then transferred to a plasma washing machine. In addition, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum deposition machine.
將以下HI-1化合物在如此製備的ITO透明電極上形成為具有1,150埃的厚度作為電洞注入層，且用濃度為1.5%的以下A-1化合物對電洞注入層進行p摻雜。將以下HT-1化合物真空沈積在電洞注入層上，由此形成膜厚度為800埃的電洞傳輸層。隨後，將以下EB-1化合物在電洞傳輸層上真空沈積成具有150埃的膜厚度，由此形成電子阻擋層。隨後，在EB-1沈積膜上以98：2的重量比真空沈積了以下RH-1化合物及以下Dp-7化合物，由此形成厚度為400埃的紅色發光層。將以下HB-1化合物在發光層上真空沈積成具有30埃的膜厚度，由此形成電子阻擋層。隨後，將以下ET-1化合物及以下LiQ化合物以2：1的重量比真空沈積於電洞阻 擋層上，由此形成厚度為300埃的電子注入及傳輸層。將氟化鋰(LiF)及鋁在電子注入及傳輸層上，依序沈積成分別具有12埃及1,000埃的厚度，由此形成負電極。 The following HI-1 compound was formed on the thus prepared ITO transparent electrode to have a thickness of 1,150 angstroms as a hole injection layer, and the hole injection layer was p-doped with the following A-1 compound at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer, thereby forming a hole transport layer with a film thickness of 800 angstroms. Subsequently, the following EB-1 compound was vacuum deposited on the hole transport layer to have a film thickness of 150 angstroms, thereby forming an electron blocking layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum deposited on the EB-1 deposited film at a weight ratio of 98:2, thereby forming a red light-emitting layer with a thickness of 400 angstroms. The following HB-1 compound was vacuum deposited on the light-emitting layer to have a film thickness of 30 angstroms, thereby forming an electron blocking layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole resistance at a weight ratio of 2:1 On the blocking layer, an electron injection and transport layer with a thickness of 300 angstroms is thus formed. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layer to have a thickness of 12 Egypt and 1,000 angstroms respectively, thereby forming a negative electrode.
在上述程序中，有機材料的沈積速率維持於0.4埃/秒至0.7埃/秒，負電極的氟化鋰及鋁的沈積速率分別維持於0.3埃/秒及2埃/秒，且沈積期間的真空度維持於2×10-7托至5×10-6托，藉此製造有機發光元件。 In the above procedure, the deposition rate of the organic material was maintained at 0.4 angstroms/second to 0.7 angstrom/second, the deposition rates of lithium fluoride and aluminum on the negative electrode were maintained at 0.3 angstroms/second and 2 angstroms/second, and the deposition rate during the deposition The degree of vacuum is maintained at 2×10 -7 Torr to 5×10 -6 Torr, thereby manufacturing an organic light-emitting device.
[實例1至實例42][Example 1 to Example 42]
除了在比較例1的有機發光元件中使用下表1中所述的 化合物代替RH-1之外，以與比較例1相同的方式製造了有機發光元件。 Except that the organic light-emitting element of Comparative Example 1 was used as described in Table 1 below An organic light-emitting element was manufactured in the same manner as in Comparative Example 1, except that the compound was substituted for RH-1.
[比較例2至比較例13][Comparative Example 2 to Comparative Example 13]
除了在比較例1的有機發光元件中，使用下表1中所述的化合物代替RH-1之外，以與比較例1相同的方式製造了有機發光元件。 An organic light-emitting element was manufactured in the same manner as in Comparative Example 1, except that in the organic light-emitting element of Comparative Example 1, the compound described in Table 1 below was used instead of RH-1.
當向實例1至實例42及比較例1至比較例13中製造的有機發光元件施加電流時，量測每一有機發光元件的電壓、效率及使用壽命(以6,000尼特計)，且其結果示於下表1中。使用壽命T95意指亮度降至其初始亮度(6,000尼特)的95%所需要的時間。 When current was applied to the organic light-emitting elements manufactured in Example 1 to Example 42 and Comparative Example 1 to Comparative Example 13, the voltage, efficiency, and service life (in 6,000 nits) of each organic light-emitting element were measured, and the results Shown in Table 1 below. Lifetime T95 means the time required for the brightness to drop to 95% of its initial brightness (6,000 nits).
當對在實例1至實例42以及比較例1至比較例13中製造的有機發光元件施加電流時，獲得表1的結果。 When a current was applied to the organic light-emitting elements manufactured in Example 1 to Example 42 and Comparative Example 1 to Comparative Example 13, the results of Table 1 were obtained.
在相關技術中廣泛使用的材料用於比較例1中的紅色有機發光元件，且紅色有機發光元件具有分別使用化合物[EB-1]及RH-1/Dp-7作為電子阻擋層及紅色發光層的結構。在比較例2至比較例13中，藉由使用C-1至C-12代替RH-1來製造有機發光元件。 A material widely used in the related art was used for the red organic light-emitting element in Comparative Example 1, and the red organic light-emitting element has compounds [EB-1] and RH-1/Dp-7 as the electron blocking layer and the red light-emitting layer, respectively Structure. In Comparative Example 2 to Comparative Example 13, organic light-emitting elements were manufactured by using C-1 to C-12 instead of RH-1.
參考表1中的結果，觀察到當使用本發明的化合物作為紅色發光層的主體時，相較於比較例中的材料而言，驅動電壓降低高達約30%，且效率增加了25%或大於25%，並且可以看到能量自主體非常好地轉移至紅色摻雜劑。此外，可以看到，在維持 高效率的同時，使用壽命特性可顯著改善了兩倍或大於兩倍。原因最終可被確定為歸因於本發明的化合物對電子及電洞的穩定性高於比較例中的化合物。 With reference to the results in Table 1, it is observed that when the compound of the present invention is used as the host of the red light-emitting layer, compared with the material in the comparative example, the driving voltage is reduced by up to about 30%, and the efficiency is increased by 25% or more. 25%, and it can be seen that the energy is transferred from the host to the red dopant very well. In addition, it can be seen that in maintaining At the same time of high efficiency, the service life characteristics can be significantly improved by twice or more than twice. The reason can ultimately be determined to be attributable to the higher stability of the compound of the present invention to electrons and holes than the compound of the comparative example.
[實例43至實例142] [Example 43 to Example 142]
除了藉由在比較例1的有機發光元件中以1：1的重量比使用下表1中所述的第一主體及第二主體來代替RH-1執行了真空共沈積之外，以與比較例1相同的方式製造了有機發光元件，以與表1相同的方式評價了每一元件的效能，且其結果示於表2中。 Except that the first host and the second host described in Table 1 below were used instead of RH-1 to perform vacuum co-deposition in the organic light-emitting element of Comparative Example 1 at a weight ratio of 1:1, in order to compare Organic light-emitting elements were manufactured in the same manner as in Example 1, and the efficacy of each element was evaluated in the same manner as in Table 1, and the results are shown in Table 2.
表2中的結果顯示出共沈積兩種類型的主體的結果，且以1：1的比率使用第一主體及第二主體的情況顯示出較僅使用第一主體時更佳的結果。可以確認，當使用第二主體時，紅色發光層中的電子及電洞維持更穩定的平衡，同時電洞的量增加，且效率及使用壽命顯著增加。 The results in Table 2 show the results of co-deposition of two types of main bodies, and the case of using the first main body and the second main body at a ratio of 1:1 shows better results than when only the first main body is used. It can be confirmed that when the second host is used, the electrons and holes in the red light-emitting layer maintain a more stable balance, while the amount of holes increases, and the efficiency and service life are significantly increased.
總之，可以確認，當使用本發明的化合物作為紅色發光層的主體時，有機發光元件的驅動電壓、發光效率及使用壽命特性可得以改善。 In conclusion, it can be confirmed that when the compound of the present invention is used as the host of the red light-emitting layer, the driving voltage, luminous efficiency, and lifespan characteristics of the organic light-emitting element can be improved.
1:基板 1: substrate
2:第一電極 2: The first electrode
3:發光層 3: luminescent layer
4:第二電極 4: second electrode
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| CN107827807A (en) * | 2017-10-23 | 2018-03-23 | 长春海谱润斯科技有限公司 | A kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device |
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| CN114096535A (en) * | 2019-11-21 | 2022-02-25 | Lt素材株式会社 | Heterocyclic compound, organic light-emitting element comprising same, composition for organic layer of organic light-emitting element, and method for producing organic light-emitting element |
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- 2020-01-21 JP JP2021539412A patent/JP7197076B2/en active Active
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- 2020-01-21 EP EP20744262.5A patent/EP3828180A4/en active Pending
- 2020-01-21 CN CN202080008817.7A patent/CN113365993B/en active Active
- 2020-01-21 TW TW109102260A patent/TWI739289B/en active
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| KR20120081539A (en) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| CN107973786A (en) * | 2016-10-25 | 2018-05-01 | 株式会社Lg化学 | New compound and utilize its organic illuminating element |
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| KR102339004B1 (en) | 2021-12-14 |
| JP7197076B2 (en) | 2022-12-27 |
| KR20200090641A (en) | 2020-07-29 |
| TW202033742A (en) | 2020-09-16 |
| US20220102646A1 (en) | 2022-03-31 |
| EP3828180A1 (en) | 2021-06-02 |
| JP2022516750A (en) | 2022-03-02 |
| CN113365993B (en) | 2024-04-05 |
| WO2020153713A1 (en) | 2020-07-30 |
| EP3828180A4 (en) | 2021-11-10 |
| CN113365993A (en) | 2021-09-07 |
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